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Ouch! Yes, doing an iCloud update with the backup…might just wipe out your outlook calendar. I just helped a client with this issue. It was easy for me as he just had a local PST for his calendar. He synched it with iTunes. I exported out the iCloud calendar in Outlook and imported back into his PST calendar. This may not be easy for you to do, but if you want help….use my online scheduler below. I can probably fix this for 30 minutes of time. I will also uninstall iCloud or reconfigure it to not use Outlook. Whatever you need, I can do!